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Angeli's salt

From Wikipedia, the free encyclopedia
Angeli's salt
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/N2O3.2Na/c3-1-2(4)5;;/q;2*+1
    Key: XDPWLJKQGUTUKZ-UHFFFAOYSA-N
  • N(=O)[N+](=O)[O-].[Na+].[Na+]
Properties
N2Na2O3
Molar mass121.991 g·mol−1
Appearancewhite solid
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Angeli's salt,sodium trioxodinitrate, is theinorganic compound with the formula Na2[N2O3]. It contains nitrogen in an unusual reduced state. It is a colorless, water-soluble solid, hence a salt. In research, this salt is used as a source of the metastablenitroxyl (HNO), which is a signalling molecule in nature.[1] It is also known by the namesodium trioxodinitrate(II) monohydrate.

Preparation and properties

[edit]

As first reported byAngelo Angeli in 1896, the salt is prepared by combining hydroxylamine and an organic nitrate, as a source ofnitronium (NO+
2
):[2][3]

NH2OH + RONO2 + 2 NaOR′ → ROH + 2 R′OH + Na2N2O3

The structure of the hydrate has been confirmed byX-ray crystallography. The anion is planar. Starting from the ONN end, the bond distances are 1.35 Å (N–O), 1.26 Å (N–N), 1.31 Å (N–Otrans), and 1.32 Å (N–Ocis). The negative charge is on the oxygen atoms at opposite ends of the molecule. The angles are 112.9° (Osingle–N–N), 118.4° (N–N–Otrans), and 122.5° (N–N–Ocis). This means that the nitrogen–nitrogen bond is adouble bond, and that thecis oxygen is slightly repelled by the single oxygen.[4]

Reaction of Angeli's salt withsecondary amines in the presence of a proton source results in extrusion of N2 viaisodiazenes as proposed intermediates.[5]

References

[edit]
  1. ^Nakagawa, H. (2013). "Controlled release of HNO from chemical donors for biological applications".J. Inorg. Biochem.118:187–190.doi:10.1016/j.jinorgbio.2012.10.004.PMID 23140899.
  2. ^Angeli, A. (1896). "Sopra la nitroidrossilammina" [On nitrohydroxylamine].Gazz. Chim. Ital. (in Italian).26:17–28.hdl:2027/hvd.cl1hem.
  3. ^Hughes, Martin N.; Cammack, Richard (1999). "Synthesis, chemistry, and Applications of Nitroxyl Ion Releasers Sodium Trioxodinitrate or Angeli's Salt and Piloty's Acid".Nitric Oxide, Part C: Biological and Antioxidant Activities. Methods in Enzymology. Vol. 301. pp. 279–287.doi:10.1016/S0076-6879(99)01092-7.ISBN 9780121822026.PMID 9919577.
  4. ^Hope, Hakon; Sequeira, Michael R. (February 1973). "Angeli's salt. Crystal structure of sodium trioxodinitrate(II) monohydrate, Na2N2O3·H2O".Inorganic Chemistry.12 (2):286–288.doi:10.1021/ic50120a008.
  5. ^Carey, Francis A.; Sundberg, Richard J. (2007).Advanced Organic Chemistry. Part B: Reactions and Synthesis (5th ed.). New York, NY: Springer.ISBN 9781601195494.OCLC 223941000.
Inorganic
Halides
Chalcogenides
Pnictogenides
Oxyhalides
Oxychalcogenides
Oxypnictogenides
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Organic
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